1600 miles round trip starting from anch..back to anch.
I'll post a map of the route later. Any input can be added & can be subject to change.

I was going to just ride up to Fairbanks then to Tok. And hit Dawson. But then that would be boring since I been up fairbank already. So might as well go explore Canada.

Hey nutty,

It looks like you will have an extra day or two before D2D, so you might consider this: Ride all the way to Watson Lake first. From Anchorage it's a 12 hour run to Haines Junction in the Yukon, then an easy 8 hours to Watson Lake from there. Good, paved road from Haines Jct to Watson Lake. You could look over the signpost forest at Watson Lake, then take a tour of Whitehorse on the way back north.

Your plan is just the opposite of what I normally do when I go to D2D, i.e. I'll ride over to Dawson City first for the get-together, then head south to Whitehorse before turning west to Alaska. I'd ride along with you, but I'm old and slow, and have to stop at every outhouse along the way. No way I could keep up.